The objective of this paper is to investigate the future evolution of port systems considering the development of major and minor ports, inter-port competition, and feasible cargo shifts resulting from improved capacity or congestion faced by ports. The literature review on port system dynamics indicates that the relationships that emerge between major and minor ports located in the range stem from competition and cooperation. However, we argue that there are essential ports that play a predominant role in shaping these relationships, while inter-port relations in the system are based on competition. With the use of transshipment forecasts, existing and emerging interdependencies among major and minor ports in the system, and capacity development and/or changes in the level of capacity utilisation, the ex-ante dynamics of the port system are evaluated. The subject of research is two port systems, namely, the Polish port system and the Rhine–Scheldt Delta port system. We investigate the future dynamics in each port system and find that the evolution pattern has different features if the minor ports improve capacity or challenge the major ports by offering free capacity. This paper contributes to research on the evolution of multi-port formations and provides new insights to the peripheral port challenge phenomenon.